Southern Highlands Beach Vacations 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Beach vacation packages in Southern Highlands

Price found within the past 48 hours. Click for updated prices.

Oaks Sydney Goldsbrough Suites

Pyrmont

$1,354

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

8.2/10 Very Good! (7,771 reviews)

Staff

Reviewed on Sep 16, 2026

Pullman Sydney Hyde Park

Darlinghurst

$1,739

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

8.6/10 Excellent! (1,001 reviews)

The location

Reviewed on Sep 12, 2026

Capella Sydney

Sydney Central Business District

$2,620

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9.8/10 Exceptional! (410 reviews)

Attention to detail was amazing. Top service and spacious room.

Reviewed on Sep 6, 2026

Medusa Boutique Hotel

Darlinghurst

$1,605

per person

Nov 5 - Nov 8

found 22 hours ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

9.6/10 Exceptional! (492 reviews)

This is the perfect hotel if you want a nice weekend away with your partner. Truly and unforgettable experience

Reviewed on Sep 11, 2026

The Capitol Hotel Sydney

Haymarket

$1,378

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (1,004 reviews)

The location is fantastic and it’s very convenient to get to the attractions, very happy with our stay.

Reviewed on Sep 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Highlands

View all trips

5* Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.

Pullman Sydney Hyde Park

Darlinghurst

$1,739

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

8.6/10 Excellent! (1,001 reviews)

The location

Reviewed on Sep 12, 2026

Capella Sydney

Sydney Central Business District

$2,620

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9.8/10 Exceptional! (410 reviews)

Attention to detail was amazing. Top service and spacious room.

Reviewed on Sep 6, 2026

The EVE Hotel Sydney

Redfern

$2,963

per person

Dec 8 - Dec 13

found 4 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9.8/10 Exceptional! (50 reviews)

Beautiful hotel with stylish interiors. It’s a shame however at the moment that they only have Olympus dining available as both Lottie and bar Julius are closed. It would also be great if you could order cocktails to the pool and not just a canned drink.

Reviewed on Sep 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Highlands

View all trips

3 Night Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,079

per person

Nov 7 - Nov 8

found 20 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

8.2/10 Very Good! (2,903 reviews)

Great location, great service. Nice rooms!

Reviewed on Sep 16, 2026

Medusa Boutique Hotel

Darlinghurst

$1,083

per person

Nov 7 - Nov 8

found 8 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9.6/10 Exceptional! (492 reviews)

This is the perfect hotel if you want a nice weekend away with your partner. Truly and unforgettable experience

Reviewed on Sep 11, 2026

Establishment Hotel

Sydney Central Business District

$1,085

per person

Nov 7 - Nov 8

found 8 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Sydney (SYD)

9/10 Wonderful! (696 reviews)

We were welcomed by Emily at Front of House who was so helpful. She gave us great recommendations and really made us welcome. My only disappointment was due to booking through Expedia only 1 breakfast was included whereas if we had booked direct both guests would receive breakfast. Otherwise the stay was ideal. The area is great, 10 minute walk to most places, circular quay, the rocks, old sydney, the shopping area in Pitt Street.

Reviewed on Sep 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Highlands

View all trips

4 Night Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.

YEHS Hotel Sydney CBD

Sydney Central Business District

$1,190

per person

Nov 9 - Nov 11

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.4/10 Very Good! (1,000 reviews)

Very central location…staff were nice. But a few warning signs on the floors advising guests to respect others and keep quiet would have been good. Was not impressed with noisy guests on my floor with little self awareness.

Reviewed on Sep 11, 2026

YEHS Hotel Sydney QVB

Sydney Central Business District

$1,230

per person

Nov 9 - Nov 11

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.6/10 Excellent! (1,004 reviews)

Staff was excellent

Reviewed on Sep 15, 2026

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,201

per person

Nov 9 - Nov 11

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to Sydney (SYD)

8.2/10 Very Good! (2,903 reviews)

Great location, great service. Nice rooms!

Reviewed on Sep 16, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Highlands

View all trips

How do I book the best Southern Highlands beach vacation packages?

Life’s a beach when you dive into our brilliant Southern Highlands beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Southern Highlands?

A rental steps from the shore creates an amazingly affordable Southern Highlands beach vacation. Seaside sojourns during low season start from $1,079. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southern Highlands beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Southern Highlands?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Southern Highlands beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Southern Highlands vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Southern Highlands beach vacation deals?

Sort your search results by deals to delight in amazing Southern Highlands beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Southern Highlands beach trip with free cancellation and/or flexible dates?

Just like the Southern Highlands tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Southern Highlands beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southern Highlands. (OK, maybe not that last part.)

Top Beach Southern Highlands Hotels

French Boutique The Loft Apartment @Chapmans+Pets+B'fast

Moss Vale NSW

15 min drive from Bendooley Estate Book Barn

Book a stay at this golf apartment in Bowral. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Moss Vale Golf Club and Leighton Gardens are ...

8.4/10 Very Good! (7 reviews)

"The Loft area worked very well for us. Two travellers and a dog. The space was very clean, the beds very comfortable, the bathroom had a great shower with lots of hot water and my granddaughter enjoyed the seperate bath each of our 4 nights. It rained our entire time and I have to sincerely thank ..."

Reviewed on Jul 10, 2026

5 star couples hideaway in the country, enjoy privacy and space - w hot tub

Penrose NSW

46 min drive from Bendooley Estate Book Barn

Stay at this cabin in Penrose. Enjoy free WiFi, a garden, and patios. Popular attractions Sylvan Glen Golf Course and Penrose Park are located nearby.

10/10 Exceptional! (11 reviews)

"Was an amazing place! Perfect in all aspects!"

Reviewed on Apr 7, 2026

The Coach House at The Rift Estate

Bowral NSW

12 min drive from Bendooley Estate Book Barn

Book a stay at this family-friendly vacation home in Bowral. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Southern Highlands Botanic ...

9.8/10 Exceptional! (10 reviews)

"Fire Place was warm. The number of rooms were perfect for our extended family. Kitchen was well-equipped. The gardens and grounds were lovely"

Reviewed on Apr 13, 2026

See all 1,641 properties in Southern Highlands

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.